The Villainy of Digger Stilles
by MusicalSensation
Summary: The second in my "Villains" series. Because he takes the word "Asshat" to a whole new low, Digger Stilles.


Let me explain what this series is. The "Villains" Series is my take on a group of characters from various shows that, honestly, I can't stand. I wanted to delve into the reasons I don't like them and possibly give them some background as to what made them the loathsome people they are. Most of the background I made up, with the exception of a few mentions of any little background tidbits that may have been said in the shows the characters are in.

This is the second in the series. I hope you enjoy.

Disclaimer: I don't own Digger. And for that, I am eternally grateful.

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**The Villainy of Jason "Digger" Stilles**

I'm an asshole.

I'm obnoxious, pompous, and I lack the charms that allow other men to pull off such traits.

When I was younger, I wanted to be a spy. Because spies are super cool and they always get the girl. I never got the girl. In fact, I think most of the girls found me repulsive. Actually, I know they found me repulsive. They'd tell me so. Daily.

They say that behind every great man, there is a woman. Well, I don't have a woman behind me, so what the hell does that say about me?

When I was a kid, my parents were consistently sending me away. Whether it was boarding school during the school year or camp during the summer. I don't remember ever seeing my parents for more than a few weeks.

One year at summer camp, I met Lorelai Gilmore. She was twelve, I was thirteen and I was in love. Granted, she wouldn't have anything to do with me. One day I saw a signup seat for the talent show the camp always put on before the all the kids went home before school started. Well, in my case it was a boarding school in Maine, but whatever. Anyway, I noticed Lorelai had signed up to sing that damn song from "Grease." What's it called? "Summer..." something or another. I noticed that Ricky Harrison had signed up to sing the song with her. Well, something had to be done about this.

It was a well know fact around camp that Ricky Harrison was allergic to peanuts. So one day I smashed up some peanuts I bought from a vending machine from when I snuck into the Counselor's lounge. I put the smashed peanut pieces in his soup during dinner, when no one was looking. The next thing you know, Ricky Harrison is breaking out into a rash and a cold sweat, and being escorted to the nurse and going home early.

When news broke that Lorelai was going to need a new partner for the duet, I felt it was my gentlemanly duty to help her out.

That was the best week ever.

Okay, so our duet sucked. Lorelai was great, but I have the singing quality of a dying cat.

Years later I was working for my father when I heard the news that Richard Gilmore was coming out of retirement to start his own business. Richard Gilmore! The father of Lorelai Gilmore! I had to get in on this.

I had no problem screwing my father over and going to Richard for a job. My father's an ass so I really didn't care.

One day I'm sitting in my office and Lorelai comes busting through the doors. She was complaining about something having to do with with her mother. I wasn't really listening that hard, but I remember how great she looked.

I remember thinking that I've gotta get this girl.

Lorelai, to my surprise, actually agreed to go out with me. The catch was that her parents couldn't know about us. And you know, if you were a 38 year old man who has as much trouble as I do getting laid, you would agree, too.

I mean, Lorelai is beautiful. She's witty, smart, and quick on her toes. And entirely to good for me. But I'm no fool. I wasn't about to let her know that.

You see, the key to keeping a girl like Lorelai when you're a guy like me is to always pretend like you're the type of guy she should be dating. Does that make any sense? In order words, give off the illusion that your her type.

Lorelai likes to talk, which is fine because I like to talk, too. The sound of my own voice is my favorite sound.

She has a daughter, which freaked me out when I found out. I'm thinking the girl's going to be, like a six year old, and children hate me, which is fine. I'm not too fond of them myself. But I didn't want the child of the woman of my dreams to hate me. Luckily, her kid was college age and a wave of relief passed through me.

The one thing I never got was Lorelai's fascination with talking about some Luke guy. She'd talk to me about her quirky little town and all the people who lived there. I'd let her talk, meanwhile I'm thinking about her in a nice French maid's uniform. For whatever reason, whenever I'd start paying attention to her, she'd be talking about something that happened with Luke, or to Luke, or about Luke.

I hate Luke.

Seriously, I wanted to know what was her hang up with this guy? She would talk about him and her voice would do this...thing. I don't know how to describe it. All I know is that her voice never did that when she talked to people about me.

As the relationship progressed, I started to worry that Lorelai was going to start losing interest.

Then one day the big boom happened. My father outed my relationship with Lorelai to her parents. And if that wasn't bad enough, Richard decided to go back to working for my father and I was out of a job.

Shit.

I needed to take matters into my own hands. I knew what I wanted to do so I called Lorelai up and asked her to meet me for some coffee.

Stupidest thing I've ever done.

I told Lorelai I was suing her father and she broke up with me.

Damn it! I honestly thought she wouldn't dump me over this. She bought me a plant, for God's sake. Mind you, it died. Quickly. But it was her gift to me and I cherished it.

Sometimes, late at night, I look at the dead plant, think of Lorelai, and I like to...Oh, I forgot what we were talking about.

Oh yeah.

She broke up with me.

I begged her not to, but apparently the idea of her boyfriend suing her father bothered her. Hell, if she wanted to sue my father, I'd probably pay for the damn lawyer.

After a few weeks of moping around my apartment, unemployed, depressed, and in desperate need of a shave, I decided that I needed to go to Lorelai and get her back.

I drove all the way to her house and knocked on the door. No answer. I decided to go to the Inn she was opening. I remember her telling me something about it opening soon, so I hoped she was there.

I enter the Inn and I look around the lobby. It seems busy but I didn't see Lorelai anywhere.

Then she walks out from the back. I can tell she was surprised to see me but I figured if she just heard me out, we'd get back together in no time.

Okay, so she was pissed to see me there, but I'm persistent. I sit in the lobby and waited. Her friend Sookie brought me out some dinner and I sat and ate and waited. I rummaged through the magazine selections and start to get bored.

Lorelai came out again and I try to convince her to sit down with me. She left and I heard her mother, Emily, come in.

Well, damn. If there was ever a woman who ever had the ability to make me wet my pants, it's Emily Gilmore.

The next thing I know, Emily's walking toward my area. She stops in her tracks when she sees me. Then Richard comes in. They mention something about hoping Lorelai had her fun, and left. I asked Lorelai if I could have their room. Her response...well, she didn't really respond. But if looks could kill...

I found myself alone in the lobby again. Some guy comes over and sits in the seat next to me. He introduced himself as Luke Danes. Luke! The man I come to think of as my archenemy.

Damn, he is good looking. Hell, if I was a woman, I'd totally tap that...I'm not going to finish that thought.

I needed to make it clear that Lorelai is all mine. Although, technically she's not, but whatever. I needed to throw this Luke guy off my game. I told him I was Lorelai's boyfriend and made it clear that we were going strong. I excused myself to go use the bathroom and left Luke.

Let me tell you, that bathroom in the Inn is nice. I just stood there for a while just looking around, examining the tile. Lovely bathroom. Lovely.

When I finally came out, I got a call. I was told that my apartment was on fire. I jumped in my car and sped home.

My apartment was not on fire.

I figured that Lorelai probably told someone to call me to get rid of me. I know when to admit defeat. I decided that maybe Lorelai and I aren't meant to be and I stopped pursuing her. It hurts, but what can you do.

Oh, and about suing her father. Let's just say my own father paid me off nicely and suggested I move away and start over.

So, here I am in Houston. I'm watching my dog as he sits by the fireplace. Sitting. Sitting. I think he's going to...nope. Sitting.

A dead plant sits atop the fireplace. Okay, not so much the plant, but the pot it came in. I had to throw the plant away when I started to notice that it was attracting bugs. But I will keep that pot forever.

I never get the girl.


End file.
